Connor McDavid’s frustration in Edmonton just raised the stakes on every decision the Leafs make with Matthews

Edmonton Oilers forward Connor McDavid (97) carries the puck around Toronto Maple Leafs forward Auston Matthews (34) during the first period at Rogers Place.
Photo credit: Perry Nelson-Imagn Images

The stress of Connor McDavid will keep teams like the Toronto Maple Leafs watching the situation play out.

Recent speculation from Edmonton Oilers columnist Gerry Moddejonge of the ‘Edmonton Journal’, he thinks that unless the Oilers prove they can be a winning team, McDavid is out the door.
Of course, it’s willful ignorance around here that fans choose to remain blind to the fact Connor McDavid could demand a trade at any point. And he is a guy who gets what he wants — unless, of course, we’re talking about bringing the Stanley Cup back to Edmonton. The harsh truth is he may end up having to go elsewhere in order to cement his legacy with the hardest trophy there is to win in professional sports.
Moddejonge isn’t an insider, and is in fact more of a football reporter, but has covered Edmonton sports for two decades with the Journal, and has covered McDavid throughout his Oilers tenure.
Edmonton has tried to make its potential most forceful bid to get over the playoff hump, trading away oft critiqued netminder Stuart Skinner to Pittsburgh for Tristan Jarry, but Jarry has been far from help, with a league low .856 SV% on the season.

The Connor McDavid trade speculation creates a new timeline for the 2027 roster reset in Toronto

Connor McDavid would go down as the greatest player to never win the Stanley Cup if he doesn’t hoist it one day, and it could speed up the process in which he leaves the Edmonton Oilers.
McDavid, as good as ever, has 40 goals, 78 assists, & 118 points in 72 games for Edmonton this season. A secondary problem, beyond McDavid, Leon Draisaitl, & Evan Bouchard, no other PPG scorers, and a lack of depth scoring in general.
Scoring has been an issue for Oilers since McDavid came to Edmonton, and including poor offensive depth, McDavid and Draisaitl have only been able to do so much.
This changes things for the Leafs timeline, as McDavid, signed until 2028 shifts the perspective on
the 2027 roster reset for what could be Toronto’s plan to wait and force their way into the Connor McDavid sweepstakes.
It does lead to a question if there is a future where both Connor McDavid and Auston Matthews are able to play together financially. This could raise the question about dealing Matthews if McDavid ever enters the table, requesting a trade out of Edmonton before his contract expires.

The Toronto organization must accelerate the pursuit of a top pairing defender to prepare for 2028

If Connor McDavid becomes the Leafs focus in 2028, they may spend this offseason on adding defense, and figuring out their future in net.
Toronto, if they want McDavid, will need to fix up the issues that have plagued Edmonton, a poor goaltending situation and a lack of depth scorers. They’ll need to build beyond a hypothetical McDavid deal.
As frustrating as the Edmonton Oilers can be, it’s not like the Toronto Maple Leafs right now are anything better. Toronto would have to convince McDavid they’re a contender, and next year will have to prove it.
The Toronto Maple Leafs, before they can even entertain Connor McDavid, need to build a team that not only can show itself to be a contender, but is built to not just rely on a single superstar.